My Favorite Organic Molecule: Trimethylxanthine

My favorite molecule is water, which goes great with my favorite organic molecule Trimethylxanthine also known as caffeine. I consume Trimethylxanthine almost every day either in coffee, tea, or chocolate. This organic molecule works on the body by blocking the breakdown of cylic adenosine monophosphate (cAMP). cAMP carries glucagon and adrenaline. Therefore when caffeine is consumed, the breakdown of cAMP does not occur, which leaves cAMP to carry more glucagon and adrenaline. The extra adrenaline then causes the heart rate to increase and blood vessels constrict (which causes an increase in blood pressure). For some people this increase in adrenaline gives them the ability to focus better because they feel more alert, for others it is more difficult to concentrate because they report feeling “jittery”.

Caffeine is a methyl group bonded to a xanthine group which gives it the following structure.   

http://www.britannica.com/EBchecked/topic/88304/caffeine

http://www.scientificamerican.com/article.cfm?id=how-does-caffeine-affect

My Favorite Organic Molecule: Fluoxetine.

Fluoxetine is my favorite organic molecule. It is better known as Prozac. It is used as an anti-depressant. I am a psychology major and am interested in all the chemical reactions that occur in the brain that cause or cure depression and anxiety, therefore this molecule is very interesting to me.

Fluoxetine was first allowed to be used for treatment in Belgium in 1986 and then a year later in the USA. However, it was first discovered in 1977 by scientists from Eli Lilly and Company. It is useful for several different kinds of psychological disorders, for example; obsessive-compulsive disorder, depression, bulimia, and panic disorder.

The way that Fluoxetine helps patients is that it regulates their serotonin levels. Serotonin is an important hormone in humans that regulates mood. Fluoxetine  is called a serotonin reuptake inhibitor (SRI) which basically means that it stops the brain from transporting serotonin away and therefore increasing the serotonin levels in the brain.

This is my attempt at drawing Fluoxetine on paint:

Sources:

http://www.reciprocalnet.org/recipnet/showsamplebasic.jsp?sampleId=27344049

http://feciklab.blogspot.com/2011/06/jesse-venturas-prozac-ignorance.html

My favorite Organic Molecule...

My favorite Organic Molecule is Alpha-tocopherol, or Vitamin E. This vitamin takes me all the way back to my childhood because my mother is an advocate for home-remedies and Vitamin E was always on her list. She said that it would help wounds, my skin, nails, and hair and to over all make me feel better. I never believed her but now that I look back I always scraped my knees and body and I don't have any scars from them. I also have healthy skin and nails. 

According to Mayoclinic.com Vitamin E exists in eight different forms, but Alpha-tocopherol is the most common and useful to humans. There is a good amount of food that contains Vitamin E like eggs, fruit, green-leafy vegetables, nuts, oils, and whole grains. So if you do not like taking pills there is other ways to get Vitamin E into your system.
Mayoclinic also states that Vitamin E does infact help your skin, hair, and nails and it helps prevents scarification. So I guess my mother's superstitions and home remedies of Vitamin E was right.

Since I have been taking Organic Chemistry I have been looking at molecules differently and Vitamin E looks very cool to me and I can understand the bonds and break it down to how it actually works a little bit better:
 

Favorite Organic Molecule: Aspirin

My favorite organic molecule is aspirin, which is also known as acetylsalicylic acid. It is one of the first pain relievers in tablet form. I chose aspirin because it is an over the counter medicine that is not only used as a pain reliever and a fever reducer but also as an inhibitor of blood clot formation. By inhibiting the production of thromboxane, aspirin has an anti-platelet effect. Under normal circumstances the antiplatelet effect binds platelet molecules together in order to create a patch of sorts on top of damaged walls of blood vessels. The platelet patch blocks blood flow downstream and locally. Which is why aspirin is used long term to help prevent strokes, blood clot formations, and heart attacks. If given immediately after a heart attack, aspirin can reduce the risk of another heart attack and/or the death of cardiac tissue. Aspirin may also be able to help prevent certain types of cancer. Aspirin is a multipurpose over the counter medicine which can be use for many reasons.

Aspirin was first synthesized by a German chemist by the name of Felix Hoffman in 1897. Hoffman knew that the basic ingredient is salicin. Salicin was used in the fifth century B.C. by Hippocrates to relieve pain and it is found in willow bark. After its eaten salicin is converted to salicylic acid by the body.  In the U.S. alone, about 40 million pounds of aspirin are sold each year. 

 
Sources:
 http://www.reciprocalnet.org/recipnet/showsamplebasic.jsp?sampleId=27344263
 http://en.wikipedia.org/wiki/Aspirin

My Favorite Molecule: ASA

My favorite organic molecule is acetylsalicylic acid (ASA), which is also known as aspirin to most people. This is my favorite molecule since it has so many usages in the healthcare world. Since I am a certified athletic trainer and nurse assistant, I find this drug helpful in many everyday situations.

Acetylsalicylic acid is a derivative of salicylate. This compound can be found in willow trees, which is important in the history of aspirin. The usage of willow tree based remedies can be dated back to 3000 BC. Archiologists have found an ancient Sumer stone tablet from the Third Dynasty of Ur that mentioned such usages of the tree. Sumer was a civilization located in Mesopotamia, which is now southern Iraq. The use of willow tree based medicine continued throughout the Ancient Greeks and Romans, and was even used by many Native American tribes in North America. In 1763 Edward Stone discovered salicylic acid, the active ingredient in aspirin. However, since salicylic acid is hard on the stomach, there was a quest to find substitute that would not hurt the stomach as much. This was accomplished in 1897 by Felix Hoffman, a German chemist who worked for the pharmaceutical company Bayer, when he discovered how to make acetylsalicylic acid.

There are many uses of aspirin, but the most common use is as an NSAID (non-steroidal anti-inflammatory drug). When used as an NSAID, it reduces swelling and relieves general pain. It is also used however as an antiplatelet, meaning that it decreases the formation of blood clots. For this reason, it is given to patients who are at risk for, or previously suffered,  a heart attack or stroke. Another thing aspirin is used for is to decrease acne. Since it is similar to salicylic acid, putting crushed aspirin on acne can reduce the irritation and help heal acne.

Overall, aspirin is a very versatile organic molecule that is important to the medical world. 

Reference: http://www.medicalnewstoday.com/articles/161255.php 

Nicotiana tabacum

Nicotiana tabacum (Nicotine) C₁₀H₁₄N₂

<sub>Nicotine is a parasympathomimetic alkaloid found in the nightshade  family of plants. It is a stimulant in mammals and historically it has been used as an insecticide.  The scientific name for tobacco was coined in honor of the French ambassador to Portugal, Jean Nicot de Villemain, who was the first to bring tobacco to Paris from the New World in 1560. In, 1828 nicotine was first isolated from the tobacco plant by Wilhelm Heinrich Posselt and Karl Ludwig Reimann.

The leaves of a tobacco plant are what are smoked, chewed or sniffed.  Tobacco, in addition to nicotine, contains more than 19 chemicals, known together as tar, that are known to cause cancer. Nicotine is a acetylcholine receptor agonist and highly addictive when coadministered with other products found in tobacco. As a parasympathomimetic drug it is known to mimick the parasympathetic nervous system having the following affects: decreases in appetite, boosts mood, increases heart rate, increases blood pressure and stimulates memory and alertness. Smokers can notice withdrawal symptoms as soon as 2-3 hours after use.. These symptoms can include: craving, anxiety, depression, drowsiness, insomnia, nightmares, headaches, increased appetite and problems concentrating.

I chose nicotine as my favorite molecule because I work at the Duke University Center for Smoking Cessation. At the Center we run studies with different types of therapies aimed at the goal of finding the best methods to help people quit smoking. According to the Center for Disease Control, 68.8% of adult smokes in the United States report they want to quit smoking and in 2010, 52.4% of adult smokers (23.7 million people) stopped smoking for more than one day. These statistics demonstrate the seriousness of how difficult it is to quit smoking and the present need for new treatments focusing on things that really work.

If anyone is interested in quitting smoking you can visit www.dukesmoking.com to find resources for quitting and also to view our current studies.</sub>

_{http://en.wikipedia.org/wiki/Nicotine.
http://www.nlm.nih.gov/medlineplus/ency/article/000953.htm
http://www.cdc.gov/tobacco/data_statistics/fact_sheets/cessation/quitting/}

My favorite organic molecule.

My favorite organic molecule is Isometheptene.  Isometheptene (also known as isometheptene mucate) is a sympathomimetic amine sometimes used in the treatment of migraines and tension headaches due to its vasoconstricting properties.  Since migraines are caused in part by a vasodialation of the blood vessels in the head, the vasoconstricting properties of Isometheptene help in counter acting this and relieving the pressure and pain caused by this.  While I am unable to find the specific origin of the compound it is evident that the vasoconstrictive properties were first recognized and utilized by drug companies to combat both migraines and tension headaches.  This drug is usually combined with both a pain reliever and a body relaxing compound. 

I am a big fan of this organic compound because I myself suffer from migraine headaches.  Tylenol and aspirin only do so much, but soon after taking this I feel a wave of calm coming over me and the migraine subsides.  The pain would be throbbing and often times due to light sensitivity.  To put the pain in perspective, I have had many occasions where the work day ends just as I slip into a migraine fit.  The first thing I would have to do is dim the dash lights because even the excess brightness was a trigger but luckily by this point the sun had gone down.  Then I would take the so called “scenic route” home just to help in avoiding the oncoming headlights and other light nuisances that are present on the highway.  Most times I would go right in to bed to block out the light and noise.  It could be 6pm, it didn’t matter to me.  Once I discovered the powers of Midrin (isometheptene containing drug), I was able to take back control of those lost evenings.  Now all I do is take a pill at the first sign and within a half hour I am back to normal.  It’s hard to believe that three different elements can combine to form such an amazing thing (C₉H₁₉N).

 

-Nicholas Manuel

 

Sources:

http://en.wikipedia.org/wiki/Isometheptene

http://www.nlm.nih.gov/medlineplus/druginfo/meds/a601064.html

http://www.drugbank.ca/drugs/DB06706

Oxytocin - Can You Feel the Love Tonight?

If you've ever experienced butterflies in your stomach at the sight of someone or felt the sensation of being head over heels, you can blame cupid or...my favorite molecule, oxytocin - "The Love Molecule".

Oxytocin is a powerful neurohormone, neuropeptide and neurotransmitter that is produced primarily in the hypothalamus that influences behavior and physiology. It was the first hormone to have its structure sequenced and synthesized in a laboratory setting in the 1953 in France and the US.

While it's often talked about for its role in promoting social bonding, it plays a large role in female reproduction especially during and after childbirth. While this is not why it is my favorite molecule, its release during labor encourages maternal bonding, facilitates birth, and instigates lactation. Once the baby is birthed, oxytocin stimulates the maternal and nurturing instincts in the mother to her baby which aids in ensuring that the baby will be taken care of instead of being neglected. It can also encourage a nurturing aspect within males and females who are not mothers.

Oxytocin is my favorite molecule due to its role in helping to establish bonds for social relationships. There is some evidence that shows that oxytocin encourages ethnocentric behavior which incorporates the empathy of in-groups with their suspicion and rejection of outsiders. In nonsexual human relationships, it is known to increase trust, generosity, and cooperation. This molecule is essentially from where friendships originate. It is not only produced during pregnancy but also when we hug or kiss a loved one which is why it plays a major role in pair bonding. It is also stimulated during sex, birth, and breast feeding.

Other noteworthy research about oxytocin is its role in autism-spectrum disorders. While research is still fairly new, studies show that there is a link between oxytocin and feelings of trust and empathy with which is a quality that those with autism have difficulty. 

References: http://www.wisegeek.org/what-is-the-function-of-oxytocin.htm, http://newdrugapprovals.wordpress.com/2013/06/07/oxytocin-the-love-molecule/

Favorite molecule: Dopamine

Dopamine is a neurotransmitter found in the brains of humans and many other animals. The first time that dopamine was synthesized was in 1910 by two scientists, George Barger and James Ewens. The name dopamine comes from the fact that it falls in the amine functional group. It's IUPAC name is 4-(2-aminoethyl)benzene-1,2-diol.

Dopamine plays a major role in the reward pathway of the brain. Essentially most rewarding behavior that has been studied has been found to increase levels of dopamine in the brain, especially in the nucleus accumbens. Increases in dopamine levels have especially been observed in activities such as eating, exercise, sexual activity, and listening to music. It has been hypothesized that the rewarding feelings that we get from dopamine have helped contribute to evolutionarily adaptive behaviors. It just so happens that many of the behaviors that are crucial to our survival also give us pleasure. Since we are rewarded by these feelings of pleasure, it is more likely that we will continue to take part in these life sustaining behaviors. Dopamine has also been linked with implicit learning which could be another contributing factor to it's effects on the reward pathway.

Diseases and conditions such as Parkinson's disease and Schizophrenia have been linked with irregularities in the dopamine system. Dopamine also has effects on the body outside of the nervous system including the digestive system and endocrine system. It is also sometimes used in order to stimulate the heart in cases were babies are born without a pulse. Certain anti-psychotic drugs have also been known to affect dopamine levels.

The reason I chose dopamine as my favorite molecule is because without dopamine giving us rewarding feelings, we might not have any favorites.

References:
 http://en.wikipedia.org/wiki/Dopamine

 http://news.discovery.com/human/psychology/music-dopamine-happiness-brain-110110.htm
 http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=681

Amoxicillin

Amoxicillin

 Given my particular interest in medicinal chemistry, amoxicillin seemed a good choice as one of my favorite organic molecules given its use as an antibiotic. I find it a particularly interesting molecule given the presence of the benzene and beta lactam ring.

  Amoxicillin

Formula: C₁₆H₁₉N₃O₅

-Functional groups present:

·      *Phenol

·      *Primary amine (basic group)

·      *Secondary amine

·      *Carboxylic acid (acidic group)

 Amoxicillin was discovered in 1972 in Beecham Research Laboratories (UK). It was discovered in an attempt to find derivatives of penicillin that could treat a wider range of infections. This led to the discovery of ampicillin followed by amoxicillin.

It is synthesized from naturally occurring substances as shown below:

2-2-(4-hydroxyphenyl)glycine                                         trimethylsylil ester of 6-APA 
chloride hydrochloride

                                                                    amoxicillin

It is an antibiotic used to fight bacteria and bacterial infections. The walls surrounding the bacteria are prevented from forming due to the presence of the amoxicillin and therefore the bacteria can no longer multiply.

Examples of bacterial infections that can be treated with amoxicillin are…

Streptococci, E. coli, Staphylococcus, H. pylori, P. mirabilis, H. influenzae, N. gonorrhoeae, and S. pneumonia.

It is due to the discovery of molecules such as amoxicillin that today we can enjoy the effective treatments of many bacterial infections.

http://www.medicalnewstoday.com/articles/158481.php

http://www.emedexpert.com/facts/amoxicillin-facts.shtml

Special K anyone?

Since I work in the emergency room, one of my favorite organic molecules happens to be the widely known drug Ketamine. When the name Ketamine is mentioned, most think of the highly abused street drug, also known as “Special K”. While the drug has a high potential for street abuse, it is one of the most unique and powerful anesthetic drugs used in hospitals and veterinary clinics across the world. Ketamine hydrochloride is a slightly acidic, non- barbiturate solution used intravenously or intramuscularly for the rapid induction of anesthesia. Ketamine is one of the few anesthetics that do not suppress breathing or require skeletal muscle relaxation when used during short surgical and diagnostic procedures, and is often referred to as a “conscious sedative”. Patients who are anesthetized with Ketamine encounter a separation of their body as they do not experience sensation or pain while the procedure is being performed, but often experience a feeling of twilight and have hallucinations. Ketamine is also the anesthetic of choice in veterinary clinics for a host of different animals, and is used as pain management therapy for animals after surgical procedures. Besides use for its anesthetic properties, Ketamine has also shown effectiveness for the treatment of depression for patients who have not responded well to other anti-depressant therapy.

Ketamine was originally developed as a less neurotoxic derivative of PCP which has a lower likelihood of producing psychotic effects. Ketamine is classified as NMDAR (n-methyl-d-aspartic acid receptor) antagonist which is a group of receptors that allow neurons to communicate through the transfer of electrical signals across the neurotransmitter. Ketamine interferes with the transmission of pain across these neurotransmitters.

IUPAC Name: 2-(o-chlorophenyl)-2-(methylamino) cyclohexanone (hydrochloride)

References:

http://www.uptodate.com/contents/ketamine-drug-information?detectedLanguage=en&source=search_result&search=ketamine&selectedTitle=1%7E100&provider=noProvider

http://www.rxlist.com/ketamine-hydrochloride-drug.htm

http://en.wikipedia.org/wiki/Ketamine

http://www.drugs.com/cdi/ketamine.html

http://www.google.com/imgres?imgurl=http://www.anesthesiawiki.net/metrohealthanesthesia/MHAnes/images/ketamine2d.jpg&imgrefurl=http://www.anesthesiawiki.net/metrohealthanesthesia/MHAnes/edu/ivanes/ketamine2.htm&usg=__GZW2-LKhb1osgK0Ilh16cH2QoFs=&h=303&w=350&sz=13&hl=en&start=3&zoom=1&tbnid=OyRAmN0mbqfJPM:&tbnh=104&tbnw=120&ei=QF8iUo_gLtCisATenoCwCQ&prev=/search%3Fq%3Dorganic%2Bchemistry%2Bof%2Bketamine%26um%3D1%26sa%3DN%26hl%3Den%26gbv%3D2%26tbm%3Disch&um=1&itbs=1&sa=X&ved=0CDAQrQMwAg

My favorite molecue: Sucrose

 

One of my favorite organic molecules is sucrose, which is known as table sugar. I love this organic molecule, because it occurs naturally in every fruit and vegetable. It is the major product of photosynthesis from sugarcane and sugar beets. The basic formula for sucrose is C₁₂H₁₂O₁₁. The glucose and fructose are joined by an oxygen bridge in the alpha orientation. It contains one six member ring of glucose and the five member ring of fructose.

 

The word sucrose came from the mid-19^th century combining the Latin word sucrum meaning sugar and the chemical suffix -ose. The history of sucrose came from a story of the army of Alexander the Great. They were halted on the banks of the river Indus and saw people in the Indian subcontinent growing sugarcane and making a powder form. Greek soldiers carried this to their mainland, however, it remained a limited crop. The product increased after the Portuguese first cultivated sugarcane in Brazil in 1532. The usage of sugar greatly increased since. It is used in tea, to bake cakes and confectionery, as well as in chocolate. 

 

 

references:

http://www.elmhurst.edu/~chm/vchembook/546sucrose.html

http://en.wikipedia.org/wiki/Sucrose

 

Retinoic Acid: My Favorite Organic Compound

          Imagine a world where no one has to worry about acne or breakouts. Wouldn't that be wonderful? Well, there is an organic compound that can and does make that dream a reality. The name is Retinoic Acid. Retinoic acid is a nutrient used and needed by the body in small does to remain in a healthy state. The growth and development of cells is often a result of this particular compound. RA (Retinoic acid) is my favorite organic compound because it has been stretched and enhanced in many laboratories, not only to treat and, in most cases, prevent acne breakouts, but it also has been recently given orally to treat acute promyelocytic leukemia, which is a cancer that has not only affected millions all over thee world, but people I know and love. This is why this compound is special to me. The U.S. National Library of Medicine and Nation Institutes of Health shows research done in France about where the origin of RA derived from. The hypothesis is that RA may be from an earlier Metazoan time period than thought previously. They came to this conclusion by noticing tissue specific roles for Retinoic acid during the development of many different species of animals. Without Retinoic acid, we wouldn't be able to function at the same healthy capacity, so it is very important for our bodies to continue its pathway of providing us this vitamin A based compound.

Sources:

Campo-Paysaa, F, F Marietaz, V Laudet, and M Schubert. PubMed. N.p., Nov. 2008. Web. 31 Aug. 2013. <http://www.ncbi.nlm.nih.gov/pubmed/19003929>.

News Medical. N.p., n.d. Web. 31 Aug. 2013. <http://www.news-medical.net/health/Retinoic-Acid-What-is-Retinoic-Acid.aspx>.

-Savannah Eliseo

Cyclosporine-Dry Eyes No More

  In the long list of molecules many jumped out as my favorite, but then I remembered something I learned when I was interning at a local Vet's office. The popular dry eye drug, Restasis, started as a veterinary medicine for treatment of the same condition in dogs. It is one of a few to make the jump from veterinary use to human use
  Cyclosporine is used as a broad anti-inflamatory and in the form of Optimmune helps to reduce damage to tear glands and help in the stimulation of tear production. It is used in dogs only to treat the condition known as keratoconjunctivitis Sica (KCS or dry eye).
  This may seem like a strange molecule to choose as my favorite, but I've seen firsthand the drug in action and how much it an improve a dog's wellbeing. My ultimate goal is to be a Veterinarian and seeing the happy smiling face of a dog treated for dry eye is very rewarding.

References:http://www.1800petmeds.com/Optimmune-prod10162.html 

                  http://www.selleckchem.com/products/Cyclosporin-A(Cyclosporine-A).html

My Favorite Organic Molecule is DNA

DNA (deoxyribonucleic acid), organic chemical of complex molecular structure that is found in all prokaryotic and eukaryotic cells and in many viruses. The nucleotide DNA consists of a deoxyribose sugar molecule to which is attached a phosphate group and one of four nitrogenous bases

·          

 

The study of DNA has developed our knowledge – DNA is the code for life. DNA encodes for proteins which make up every living organism – whether it be plant, animal or bacteria. Understanding what parts of the DNA encode for which proteins is important – by studying DNA we’ve been able to figure out genes responsible for many things – everything from why some flowers are certain colors to which parts of our DNA are responsible for hair color and everything in between. Furthermore by studying DNA, we have been able to figure out much about evolution and how species evolve – in particular sorting out how different plants and animals are related to each other.

Understanding how DNA mutates, changes and replicates is also important, as it can inform us about the underlying mechanisms that cause DNA to change. Figuring out the variations between people that occur in our DNA t is also really interesting – finding where the differences occur in the genome and why DNA varies between people and animals can lead to understanding why people are different and the environmental triggers that can lead to changes in our DNA and consequent function of a gene. And it is has key importance in forensic biology – the sequences of DNA that vary from person to person is what we target when we want to use DNA to identify people.

And finally by studying DNA, we have been able to characterize much about disease. A really well known example of the importance of DNA and knowing about it, has been the discovery of the BRCA gene mutations that increase the risk of breast cancer in women. By being able to understand how DNA replicates, mutates and what the final result of this has really improved our knowledge about biological organisms. Knowledge about DNA is used in many areas of biology, so it has a very important role to play in not only just in understanding the world around us, but also for improving health and conserving the environment.

I, like many people, had trouble choosing a favorite organic molecule.  I decided to go with a molecule that has a great impact on my day to day life: sentraline.  Sentraline is what is known as an ssri, a selective serotonin reuptake inhibitor.    It works by affecting activity in the brain (specifically serotonin levels) in order to treat illnesses like depression and obsessive compulsive disorder.  Like any drug, it does not work for everyone, and can have side effects ranging from psychological (e.g. suicidal thoughts) to physical (like nausea).  However, speaking from personal experience, if one does not experience severe (or any) side effects it can make a huge difference concerning the treated disorder.  Though development of the drug was begun as early as 1971 by various chemists working for the Pfizer company , it was not FDA approved until 1991.   More than 40 years later, the drug is still going strong, with a generic version becoming available in 2006.

Sources:

http://www.nlm.nih.gov/medlineplus/druginfo/meds/a697048.html

http://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0012108/

http://en.wikipedia.org/wiki/Sertraline